Vol. 70
NOTES
428
pounds into line with the corresponding waters and ammonias.
the length of the column was calibrated in mm. (0, bottom; 100 mm., top). Checks were obtained in duplicate runs. Comparative data on DEPARTMENT OF CHEMISTRY UNIVERSITY OF CALI PORN^ the relative adsorption of the indicators on Silene BERKELEY, CALIFORNIA RECEIVEDJULY 1, 1947 EF-Alumina-Celite 535 (5 :5 :2 by weight) are also presented. It is interesting to note that the highly polar Chromatography of Some Common Indicators dyes, e. g,, the sodium salts are more strongly adsorbed. BY J. V. KARABINOS~ AND P. M. HYDE CIEMICU LABOMTORY
Alumina,2 calcium carbonate, talc, Super Cel UNIVERSITY OF h N hANCISC0 CALIFORNIA and HyAo Super Cel have been used successfully S A N FRANCISCO, RECEIVED JUNE 30,1947 as adsorbents for the chromatography of coal tar dyes and indicators.g We wish to add to this list Silene EF4 which has already found extensive use Preparation of Resacetophenone in the carbohydrate s e r i e ~ . ~ BY JOSEPH R. KILLELEAAND H. G. LINDWALL The relative degree of adsorption of the indicators on Silene EF-Celite 5356 (5: 1 by weight) The zinc chloride method commonly employed was determined as follows. The indicator (0.75 for the preparation of resacetophenone' involves a mg.) dissolved in 0.4 ml. of 90% dioxane (90 ml. vacuum distillation and yields 65% of colored dioxane-10 ml. water) was put on a Tswett colproduct. Since the vacuum distillation of highumn (10 X 100 mm.) previously wetted with 0.5 melting solids is a troublesome process, we have ml. of the solvent and the indicator was develadopted a boron fluoride method which eliminates oped with 5.0 ml. of 90% dioxane. The position the. necessity of the distillation and gives superior of the colored zone was easily determined since yields of colorless product. Details are given below. TABLE I RELATIVEDEGREE OF ADSORPTION OF SOME INDICATORSA mixture of resorcinol, 55.0 g. (0.5 mole), acetic anhydride, 54.5 g. (50.0 ml., 0.53 mole) and commercial Position of zone, mm. (color) anhydrous ether, 75 ml., is saturated with gaseous boron Indicator Silene EF Silene BF-Alumina fluoride in an ice-bath. The mixture is then stored in a Aurin tricarboxylic acid, refrigerator for ninety-six hours. The heavy, yellow crystalline mass is broken up with a glass rod and the ammonium salt 99-100 (Br) 99-100 (Br) contents, of the flask transferred to a beaker containing Indigo carmine 99-100 (BI) 99-100 (BI) 200 g. of crushed ice. The ether is distilled off on a water98-100 (R) Alizarin red S 98-100 (R) bath or allowed to evaporate in a good hood. The light Alizarin yellow R 98-100 (Y) 98-100 (Y, yellow solid is washed with cold water. It weighs 73.0 g . (96%) and melts at 138-142'. I t may be recrystalMethyl violet 60-93 (BI) 68-100 (BI) 97-98 (Y-0) lized from 1200 ml. of boiling water (Norit), the recovery Dichlorofluorescein 91-96 (0) being 69.0 g. of colorless solid (91%) melting at 144-145'. Congo red 85-90 (R) 97-100 (0). A mixed melting point of this product with a sample Brom phenol blue 95-99 (P) 73-80 (PI prepared by the zinc chloride method showed no depression. The dibenzoate, prepared by Baker's method' BrcJm cresol green 62-70 (Bl) 96-99 (BI) melted a t 80-81" mixed wit! the dibenzoate prepared Chlor phenol red 95-98 (P) 60-70 (P) from Cooper's product, 80-81 65-75 (P) Brom cresol purple 15-25 (P) The boron fluoride method exemplified above m-Cresolsulfonphthalein 1,525 (Y) 57-63 (0) has been employed, with slight modifications, in Methyl orange 5-20 (Y) 51-60 ( Y ) this Laboratory for the preparation of other polyTropaeolin 00 8-18 (Y) 45-55 (Y) hydroxyacetophenones. o-Cresolphthalein 8-18 (Y) 47-55 (Y) (1) Cooper, "Org. Syn.," 31, 103 (1941). Thymol blue 0-10 (Y) 25-35 (Y) (2) Baker, J. Chcm. SOC.,1884 (1933). Cresol red 8-15 (Y) 48-52 (Y) Brom thymol blue 0-2 (Y) Waa. H. NICHOLSLABORATORY 0-4 (Y) NEW Yo- UNIVERSITY 0 m-Nitrophenol 0 ~JNIVERSITY HEIGHTS Phenolphthalein 0 0 RECEIVED AUGUST9, 1947 NEWYORK53, N. Y.
.
(1) Present address: Department of Chemistry, St. Procopius College, Lisle, Illinois. (2) C. P. grade. J. T. Baker Chemical Company, Philliprburg, New Jersey. (3) P. Ruggli and 1'. Jensen, Hclo. Chim. Acta, 18, 624 (1934); 19, 64 (1936); P. Ruggli and M. Stauble, ibid., P I , 689 (1940); H. H. Strain, THISJOURNAL, 61, 1292 (1939); W. Rieman, J. Chcm. Ed., 18, 131 (1941). (4) A commercial hydrated calcium silicate generously supplied by the Columbia Chemical Division, Pittsburgh Plate Glass Co.,
Barberton, Ohio. (5) L. W. Georges, R. S. Bower and M. L. Wolfrom, THIS JOURNAL,
68,2169 (1946).
(6) Johns-Manville
Co.. New
York, N. Y.
Vanadium Oxide, a Hydrogenation Catalyst] BY V. 1. KOMAREWSKY, L. B. Bos
AND
J. R. COLBY
Vanadium oxide is widely used as an oxidation catalyst. It has also been reported to be an effective catalyst for the dehydrogenation of hydro(1) Presented before the Division of Petroleum Chemistry at the Atlantic City Meeting of the American Chemical Society, April 14, 1947.
